Phenol, 4-methoxy-3-nitro-, 1-acetate → 1,4-Benzenediol, 2-nitro-

HRID 280819Notes

Reaction equation

HRID 280819 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10]C(=O)C)[CH:7]=[CH:6][C:5]=1[O:14]C)([O-:3])=[O:2]>Br>[N+:1]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 15676975Phenol, 4-methoxy-3-nitro-, 1-acetate

Product 1

HCID 43139181,4-Benzenediol, 2-nitro-

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The 2-nitro-4-acetyloxyanisole (160 g, 0.757 mole) in 47% aqueous hydrobromic acid (1,200 ml) was refluxed for 1 hour. The resulting solution was evaporated under vacuum to 200 ml. The 2-nitrohydroquinone (115 g, 78%) separated on cooling as orange prisms.

Workup

  1. customThe resulting solution was evaporated under vacuum to 200 ml
  2. customThe 2-nitrohydroquinone (115 g, 78%) separated
  3. temperatureon cooling as orange prisms

Sources & evidence

ORD record
ord-b05c22bbb41448e5815841a40ae78cd7
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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